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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:34:39 UTC
Update Date2019-07-23 06:23:34 UTC
HMDB IDHMDB0037340
Secondary Accession Numbers
  • HMDB37340
Metabolite Identification
Common NameCosmosiin
DescriptionCosmosiin, also known as apigenin 7-O-glucoside or apigetrin, is a member of the class of compounds known as flavonoid-7-O-glycosides. Flavonoid-7-O-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Cosmosiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cosmosiin can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Cosmosiin can also be found in dandelion coffee and in Teucrium gnaphalodes (Wikipedia). Cosmosiin can also be found plants such as wild celery and anise. Cosmosiin has been shown to exhibit anti-platelet function (PMID: 21834233 ).
Structure
Data?1563863014
Synonyms
ValueSource
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranosideChEBI
7-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
7-O-beta-D-Glucosyl-5,7,4'-trihydroxyflavoneChEBI
Apigenin 7-O-glucosideChEBI
ApigetrinChEBI
CosmetinChEBI
CosmosiinChEBI
CosmosiosideChEBI
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl b-D-glucopyranosideGenerator
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl β-D-glucopyranosideGenerator
7-(b-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneGenerator
7-(Β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneGenerator
7-O-b-D-Glucosyl-5,7,4'-trihydroxyflavoneGenerator
7-O-Β-D-glucosyl-5,7,4'-trihydroxyflavoneGenerator
4',5,7-Trihydroxyflavone 7-beta-D-glucosideHMDB
4',5,7-Trihydroxyflavone 7-β-D-glucosideHMDB
7-O-beta-D-GlucopyranosylapigeninHMDB
7-O-beta-D-GlucosylapigeninHMDB
7-O-Β-D-glucopyranosylapigeninHMDB
7-O-Β-D-glucosylapigeninHMDB
Apigenin 7-beta-D-glucosideHMDB
Apigenin 7-beta-glucopyranosideHMDB
Apigenin 7-glucosideHMDB
Apigenin 7-O-beta-D-glucopyranosideHMDB
Apigenin 7-O-beta-D-glucosideHMDB
Apigenin 7-O-beta-glucopyranosideHMDB
Apigenin 7-O-beta-glucosideHMDB
Apigenin 7-O-β-D-glucopyranosideHMDB
Apigenin 7-O-β-D-glucosideHMDB
Apigenin 7-O-β-glucopyranosideHMDB
Apigenin 7-O-β-glucosideHMDB
Apigenin 7-β-D-glucosideHMDB
Apigenin 7-β-glucopyranosideHMDB
Apigenin-7-glucosideHMDB
CosmociinHMDB
CosmosideHMDB
CosmosiineHMDB
Apigenin-7-D-glucosideMeSH
Apigenin-7-O-beta-D-glucopyranosideMeSH
Chemical FormulaC21H20O10
Average Molecular Weight432.381
Monoisotopic Molecular Weight432.105646844
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Nameapigenin 7-o-β-glucoside
CAS Registry Number578-74-5
SMILES
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1
InChI KeyKMOUJOKENFFTPU-QNDFHXLGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.97 g/LALOGPS
logP0.68ALOGPS
logP0.44ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.06 m³·mol⁻¹ChemAxon
Polarizability42.1 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014r-0101900000-f6718e10f3de7520652fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014r-0101900000-f6718e10f3de7520652fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014r-0101900000-f6718e10f3de7520652fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-014r-0101900000-f6718e10f3de7520652fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-014i-0090000000-eedd23913ab9497a0eacJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-001i-0000900000-e2260ea719dbee112e94JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0190800000-d6fb1bf837b7e2f19b9bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-be62ac4071bbf231aebbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-2290000000-45b3c356a68218e5c2dbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-1151900000-829923d6de81818f47a3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1090200000-a27b90fa5b842325e59dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3290000000-4e0d09fb8af7034a03ebJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003911
KNApSAcK IDC00001017
Chemspider ID4532607
KEGG Compound IDC04608
BioCyc IDAPIGENIN-7-O-BETA-D-GLUCOSIDE
BiGG IDNot Available
Wikipedia LinkApigetrin
METLIN IDNot Available
PubChem Compound5280704
PDB IDNot Available
ChEBI ID16778
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chaves DS, Frattani FS, Assafim M, de Almeida AP, de Zingali RB, Costa SS: Phenolic chemical composition of Petroselinum crispum extract and its effect on haemostasis. Nat Prod Commun. 2011 Jul;6(7):961-4. [PubMed:21834233 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .